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[ CAS No. 3385-21-5 ] {[proInfo.proName]}

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Chemical Structure| 3385-21-5
Chemical Structure| 3385-21-5
Structure of 3385-21-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3385-21-5 ]

CAS No. :3385-21-5 MDL No. :MFCD00059563
Formula : C6H14N2 Boiling Point : -
Linear Structure Formula :- InChI Key :GEQHKFFSPGPGLN-UHFFFAOYSA-N
M.W : 114.19 Pubchem ID :18814
Synonyms :

Safety of [ 3385-21-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P301+P312-P303+P361+P353-P304+P340-P305+P351+P338-P310 UN#:2735
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 3385-21-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3385-21-5 ]

[ 3385-21-5 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 3971-31-1 ]
  • [ 3385-21-5 ]
  • 2
  • [ 3385-21-5 ]
  • [ 216699-86-4 ]
  • <i>N</i>-(6,7-dimethoxy-quinoxalin-2-yl)-cyclohexane-1,3-diamine [ No CAS ]
  • 3
  • [ 3385-21-5 ]
  • [ 37091-73-9 ]
  • N1,N3-bis(1,3-dimethylimidazolidin-2-ylidene)cyclohexane-1,3-diamine [ No CAS ]
  • 4
  • [ 3971-31-1 ]
  • [ 3385-21-5 ]
  • 5
  • [ 34619-03-9 ]
  • [ 3385-21-5 ]
  • [ 347186-01-0 ]
YieldReaction ConditionsOperation in experiment
92% In chloroform; at 20℃; A solution of di-tert-butyl dicarbonate (14.3 mg, 65.5 mmol) in chloroform (210 ml) was added dropwise to a solution of 1,3-diaminocyclohexane (15.0 g, 131 mmol) in chloroform (300 ml), and the resulting mixture was stirred overnight at room temperature. After completion of the reaction, the precipitate was removed. The solvent was distilled off from the filtrate under reduced pressure, and the residue was purified by a silica gel chromatography (eluent: chloroform/methanol) to obtain tert-butyl 3-aminocyclohexanecarbamate (13.0 g, yield 92%).
  • 6
  • [ 24424-99-5 ]
  • [ 3385-21-5 ]
  • [ 347186-01-0 ]
YieldReaction ConditionsOperation in experiment
In chloroform; at 0 - 20℃; for 16h; 3-Diaminocyclohexanediamine (25 g) was dissolved in chloroform (500 ml), added with di-t-butyl dicarbonate (23.9 g) with stirring and ice cooling and stirred at room temperature for 16 hours. The solvent of the reaction mixture was evaporated under reduced pressure, and the residue was added with dichloromethane and saturated aqueous sodium carbonate for extraction. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (chloroform:methanol:triethylamine=100:10:1) to obtain the title compound (16 g).
  • 7
  • [ 1810-72-6 ]
  • [ 3385-21-5 ]
  • [ 1000417-94-6 ]
YieldReaction ConditionsOperation in experiment
36.3% With pyridine; for 48h;Heating / reflux; a) N-(6-chloroquinolin-2-yl) cyclohexane-1, 3-diamine; <strong>[1810-72-6]2,6-dichloroquinoline</strong> (198 mg, 1.0 mmol, ) and cyclohexane-1, 3-diamine (457 mg, 4.0 mmol) were refluxed in pyridine (10 mL) for 48 h. The solvent was evaporated and the residue was purified on a pre-packed SiO2-column (Isolute, 10 g) eluted with DCM: MeOH (containing 1 % NH40H aq) 10: 1 to yield 100 mg (36. 3 %) of the title compound. IH NMR (500 MHz, MeOH-d4) 8 7.72-7. 67 (m, 1H), 7.55-7. 50 (m, 2H), 7.41-7. 38 (m, 1H), 6.80 (d, 1H, minor isomer), 6.71 (d, 1H, major isomer), 4.38 (bs, 1H, minor isomer), 3.98 (m, 1H, major isomer), 3.04 (m, 1H, minor isomer), 2.79 (m, 1H, major isomer), 2.25-1. 01 (m, 8H).
  • 8
  • [ 5900-58-3 ]
  • [ 124-09-4 ]
  • [ 5162-44-7 ]
  • [ 446-48-0 ]
  • [ 7209-38-3 ]
  • [ 74-96-4 ]
  • [ 4784-77-4 ]
  • [ 22288-78-4 ]
  • [ 542-69-8 ]
  • bromomethyl resin [ No CAS ]
  • 9-fluorenyl-methoxycarbonyl-cyclohexyl alanine [ No CAS ]
  • [ 462-94-2 ]
  • [ 1458-98-6 ]
  • [ 78-77-3 ]
  • [ 1809-10-5 ]
  • [ 110-53-2 ]
  • [ 592-55-2 ]
  • [ 7328-91-8 ]
  • [ 871-76-1 ]
  • [ 105-83-9 ]
  • [ 144-48-9 ]
  • [ 929-59-9 ]
  • [ 107-59-5 ]
  • [ 5324-30-1 ]
  • [ 5428-54-6 ]
  • [ 27129-86-8 ]
  • [ 2417-72-3 ]
  • [ 2581-34-2 ]
  • [ 554-84-7 ]
  • [ 3385-21-5 ]
  • [ 126-38-5 ]
  • [ 636-93-1 ]
  • [ 88-30-2 ]
  • [ 620-13-3 ]
  • [ 823-78-9 ]
  • [ 5035-82-5 ]
  • [ 29022-11-5 ]
  • [ 539-48-0 ]
  • [ 35661-39-3 ]
  • [ 26759-46-6 ]
  • [ 20439-47-8 ]
  • [ 2615-25-0 ]
  • [ 6393-01-7 ]
  • [ 5372-81-6 ]
  • [ 35661-40-6 ]
  • [ 100-39-0 ]
  • [ 611-17-6 ]
  • [ 23915-07-3 ]
  • [ 71989-23-6 ]
  • [ 35737-15-6 ]
  • [ 2592-95-2 ]
  • [ 18880-00-7 ]
  • [ 88681-68-9 ]
  • [ 100063-22-7 ]
  • [ 75-03-6 ]
  • [ 106-94-5 ]
  • [ 104-81-4 ]
  • [ 589-10-6 ]
  • [ 107-15-3 ]
  • [ 109-76-2 ]
  • [ 110-60-1 ]
  • [ 7051-34-5 ]
  • [ 106-95-6 ]
  • [ 622-95-7 ]
  • [ 589-15-1 ]
  • [ 134-20-3 ]
  • [ 2550-36-9 ]
  • [ 89-92-9 ]
  • [ 456-41-7 ]
  • [ 766-80-3 ]
  • [ 459-46-1 ]
  • [ 874-98-6 ]
  • [ 402-49-3 ]
  • [ 870-63-3 ]
  • [ 85118-01-0 ]
  • [ 22115-41-9 ]
  • [ 3958-57-4 ]
  • [ 100-11-8 ]
  • [ 107-82-4 ]
  • [ 6482-24-2 ]
  • [ 3132-64-7 ]
  • [ 112883-41-7 ]
  • [ 3433-80-5 ]
  • [ 52727-57-8 ]
  • C18H15N2O3PolS [ No CAS ]
  • C20H20N3OPolS [ No CAS ]
  • C23H19N2O2PolS [ No CAS ]
  • C18H23ClN3OPolS [ No CAS ]
  • C22H26N3OPolS [ No CAS ]
  • C22H23N2O5PolS [ No CAS ]
  • C20H26ClN2O3PolS [ No CAS ]
  • C23H22ClN2O3PolS [ No CAS ]
  • C20H21FN3O3PolS [ No CAS ]
  • C22H29N2O3PolS [ No CAS ]
  • C21H28N3O3PolS [ No CAS ]
  • C19H26N3O4PolS2 [ No CAS ]
  • C22H30N3OPolS [ No CAS ]
  • C21H28N3O4PolS [ No CAS ]
  • C26H26N3OPolS [ No CAS ]
  • C23H15ClF3N2O2PolS [ No CAS ]
  • C24H22N3O3PolS [ No CAS ]
  • C23H16ClF2N2O2PolS [ No CAS ]
  • C22H22Br2N3OPolS [ No CAS ]
  • C24H26FN2O5PolS [ No CAS ]
  • C25H22FN2O4PolS [ No CAS ]
  • C26H22N3O4PolS [ No CAS ]
  • C25H25ClN3O3PolS [ No CAS ]
  • C25H18ClF2N2O3PolS [ No CAS ]
  • C29H26N3O3PolS [ No CAS ]
YieldReaction ConditionsOperation in experiment
With piperidine; Carbonyldiimidazole; tin-2-ethylhexanoate dihydrate; potassium tert-butylate; water; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; diisopropyl-carbodiimide; dibromotriphenylphosphorane; In DMF (N,N-dimethyl-formamide); dichloromethane; N,N-dimethyl acetamide; 1,2-dichloro-ethane;Combinatorial reaction / High throughput screening (HTS); EXAMPLE 1 [0213] This example shows the synthesis of a combinatorial library of thioquinazolinone derivatives. [0214] Step 1a: Preparation of Wang Bromide Resin [0215] 40 tea bags containing 2 g each of Wang resin (80 g, 120 mmol) was taken in a 5 L PP container. A solution of triphenylphosphine dibromide (152 g, 0.15 M, 3 eq., 360 mmol) in 2000 ml DCM was added and the solution was shaken at room temperature overnight. The resin was sequentially washed with DCM (4×, 1.5 L each) and diethylether (6×, 1.5 L each) and dried under vacuum, to give the bromo wang resin. [0216] Step 1b: Loading of the Nitrophenol on Bromo Wang [0217] 20 g of the Bromo wang resin (1.5 meq/g) was taken in a 2 L wide-mouthed glass container and 1000 mL DMA was addded to it followed by the addition of the nitro phenol (10 eq., 0.3M, 300 mmol). Potasium t-butoxide (33.46 g, 10 eq., 300 mmol) was then added to it and the bottles were heated at 50 C. overnight. The bags were washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The tea bags were then dried overnight in air. The following nitrophenols were used: [0218] 2-METHYL-5-NITROPHENOL [0219] 5-HYDROXY-2-NITROBENZOTRIFLUORIDE [0220] 3-METHYL-4-NITROPHENOL [0221] 2-METHOXY-5-NITROPHENOL [0222] M-NITROPHENOL [0223] Step 1c: Reduction of the Nitro Group to Amine [0224] A 2.0 M solution of tin-2-ethylhexanoate dihydrate was prepared in DMF containing 0.5% H2O. The tea bags were added and the solution is heated at 50 C. for 40 hours. After cooling the bags are washed with DMF/10% HOAc (3×), DMF (3×), 5% DIEA/DCM (2×), DCM (2×) and MeOH (2×) and dried in air overnight. [0225] Step 1d: Coupling N-FMOC Protected Amino Acid to Wang Resin. [0226] 20 g of Wang resin (1.5 meq/g) was placed in a porous polypropylene packet (Tea-bag, 60 mm×60 mm, 65mu) and taken in a 1000 mL plastic bottle. DMF (300 mL), DCM (300 mL), FMOC-Cyclohexyl alanine (70.82 g, 6 eq., 0.3M, 180 mmol), DIC (22.71 g, 6 eq., 180 mmol), HOBt (24.32 g, 6 eq., 180 mmol) were added sequentially. After shaking for 12 hours, the packet was washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The packet was then dried overnight in air. The tea bags containing the amino acids were then treated with 20% piperidine/DMF for 2 h at room temperature to deblock the FMOC group. The following amino acids were used: [0227] FMOC-GLY-OH [0228] FMOC-ALA-OH [0229] FMOC-L-ISOLEUCINE [0230] FMOC-L-PHENYLALANINE [0231] FMOC-D-NLE-OH [0232] FMOC-CHA-OH [0233] FMOC-L-TRYPTOPHAN [0234] Step 1e: Coupling of the Diamines to Wang Resin [0235] 20 g of Wang resin (1.5 meq/g) was placed in a porous polypropylene packet (Tea-bag, 60 mm×60 mm, 65mu) and taken in a 1000 mL Nalgene bottle. 600 mL of DCM was added followed by the addition of the carbonyl diimidazole (29.9 g, 6 eq., 0.3M, 180 mmol) and the flasks were shaken at room temperature for 3 hours after which they were decanted and washed with DCM (2×, 600 mL). To these Nalgene bottles were added the diamines (6 eq., 0.4M, 180 mmol) in 450 mL of DCM (0.4M) and they were shaken at room temperature overnight. The diamines used were as follows: [0236] 2,2-DIMETHYL-1,3-PROPANEDIAMINE [0237] 1,3-CYCLOHEXANEDIAMINE [0238] (1R,2R)-(-)-1,2-DIAMINOCYCLOHEXANE [0239] TRANS-1,4-DIAMINOCYCLOHEXANE [0240] P-XYLYLENEDIAMINE [0241] 1,4-BIS(3-AMINOPROPYL)PIPERAZINE [0242] ETHYLENEDIAMINE [0243] 1,3-DIAMINOPROPANE [0244] 1,8-DIAMINO-3,6-DIOXAOCTANE [0245] 1,4-DIAMINOBUTANE [0246] 1,5-DIAMINOPENTANE [0247] 1,6-HEXANEDIAMINE [0248] N,N-BIS(3-AMINOPROPYL)METHYLAMINE [0249] 2,2'-THIOBIS(ETHYLAMINE) [0250] 2,5-DIMETHYL-1,4-PHENYLENEDIAMINE [0251] After shaking overnight, the packets was washed alternatively with DMF (500 mL) and DCM (500 mL) 3 cycles followed by 6 cycles of MeOH (500 mL). The packet was then dried in air. [0252] Step 2: Formation of the Isothiocyanate [0253] The o-amino benzoate ester (136 g, 10 eq., 900 mmol) was taken in a 5 L wide-mouthed glass bottle and 2.7 L of dichloroethane was added to it (0.3M). The following esters were used: [0254] METHYL ANTHRANILATE [0255] METHYL 2-AMINO-4-CHLOROBENZOATE [0256] 2-AMINO-4,5-DIMETHOXYBENZOIC ACID [0257] METHYL ESTER [0258] METHYL 3,4,5-TRIMETHOXYANTHRANILATE [0259] DIMETHYL AMINOTEREPHTHALATE [0260] METHYL 2-AMINO-5-BROMOBENZOATE [0261] METHYL 3-AMINOTHIOPHENE-2-CARBOXYLATE [0262] METHYL 3-AMINO-5-PHENYLTHIOPHENE-2-CARBOXYLATE [0263] Thiocarbonyl diimidazole (160 g, 10 eq., 900 mmol) was added to it and the solution was heated at 55 C. overnight to form the isothiocyanate. [0264] Step 3: Formation of the Thioquinazolinone [0265] The next day the tea bags containing the amino acids, diamines and the amino phenols on wang resin (90 mmol) was added to the isothiocyanate solution from reaction 2 and the glass bottles were heated at 55 C. overnight. After cooling the bags was washed alternatively with DMF (2000 mL) and DCM (2000 mL) 3 cycles followed by 6 cycles of MeOH...
  • 9
  • [ 347186-01-0 ]
  • di-tert-butyl dicarbonate {(BOC)2O} [ No CAS ]
  • [ 3385-21-5 ]
  • [ 27738-96-1 ]
  • [ 390765-51-2 ]
YieldReaction ConditionsOperation in experiment
13% In cyclohexanone; toluene; a tert-butyl 3-(2,4-dioxo-3,4, 5,6,7,8-hexahydro-1(2H)-quinazolinyl)cyclohexylcarbamate A solution of 2.13 ml (20.53 mmol) of cyclohexanone and 4.0 g (18.66 mmol) of <strong>[347186-01-0]tert-butyl 3-aminocyclohexylcarbamate</strong> [prepared from 1,3-diaminocyclohexane and di-tert-butyl dicarbonate {(BOC)2O}] in 300 ml of toluene is treated with a spatula tip of camphorsulphonic acid and boiled for 1.5 hours, with the use of a Dean-Stark separator. The mixture is allowed to cool to room temperature, and 1.8 ml of chlorocarbonyl isocyanate are added. The mixture is again heated at reflux. After 45 minutes, the reaction has ended. Most of the toluene is removed using a rotary evaporator and the residue is diluted with dichloromethane. The mixture is washed with saturated sodium bicarbonate solution and dried over sodium sulphate. The mixture is concentrated using a rotary evaporator and the residue is purified by column chromatography (silica gel, cyclohexane/ethyl acetate 1:2). The product fraction is freed from the solvent and the residue is recrystallized from ethyl acetate. This gives 900 mg (2.48 mmol, 13% yield) of a white solid which is a cis/trans isomer mixture. Melting point: >240 C. Rf value: 0.46 (ethyl acetate/methanol 4:1). 1H-NMR (300 MHz, DMSO-d6, delta/ppm): 10.96 (1H, s), 6.81 (1H, d), 3.91-3.79 (1H, m) 3.40-3.24 (1H, m, partially obscured by the signal for water), 2.53-2.47 (2H, m, partially obscured by the signal for DMSO), 2.49-2.24 (2H, m), 2.21 (2H, t), 1.76-1.63 (6H, m), 1.58-1.48 (4H, m), 1.37 (9H, s). MS (ESI): 749.4 (2M+Na+), 727 (2M+H+), 386.1 (M+Na+), 364 (M+H+).
  • 10
  • [ 3385-21-5 ]
  • [ 1197953-49-3 ]
  • [ 1407520-08-4 ]
YieldReaction ConditionsOperation in experiment
68% With hydrogenchloride; In ethanol; 2-methoxy-ethanol; at 110℃;Sealed tube; Step 1 : Synthesis of 17Compound 2 (158mg, 0.50 mmol), 1 ,3-diaminocyclohexane (57.1 mg, 0.5mmol) was dissolved in methoxyethanol (1 .6 mL) in a sealed tube and HCl/EtOH (200 mu) was added. The content was heated at 1 10 C overnight. Solvent was removed in vacuo and the residue was purified by 2 prep-TLC plate (360 mL DCM/24 mL MeOH/12 mL 7N NH3.MeOH) to give final product as a light colored solid (134 mg, yield 68 %).
68% In 2-methoxy-ethanol;Sealed tube; Compound 2 (158mg, 0.50 mmol), 1 ,3-diaminocyclohexane (57.1 mg, 0.5mmol) was dissolved in methoxyethanol (1.6 mL) in a sealed tube and HCI/EtOH (200 muIota) was added. The content was heated at 110 C overnight. Solvent was removed in vacuo and the residue was purified by 2 prep-TLC plate (360 mL DCM/24 mL MeOH/12 mL 7N NH3.MeOH) to give final product as a light colored solid (134 mg, yield 68 %).
  • 11
  • [ 779353-64-9 ]
  • [ 3385-21-5 ]
  • N1-(5-chloro-3-ethylpyrazolo[1,5-a]pyrimidin-7-yl)cyclohexane-1,3-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% With N-ethyl-N,N-diisopropylamine; In isopropyl alcohol; at 85℃; for 2h; Example 27 N-(3-(3-ethyl-5-( (S)-2-(2-hydroxyethyl)piperidin-l-yl)pyrazolo[l, 5- ajpyrimidin- 7-ylamino)cyclohexyl)acrylamide (MFH-1-167-1) Nl-(5-chloro-3-ethylpyrazolo[l,5-a]pyrimidin-7-yl)cyclohexane-l,3-diamine (MFH-1-151- 1) The mixture of SM-1-49-1 (300 mg, 1.388 mmol), SM-1-167-1 (500 mg, 4.442 mmol), DIPEA (270 mg) and i-PrOH (5 mL) was stirred at 85 C for 2 h. After completion, the reaction was concentrated to remove the solvent and the residue was purified by silica gel (NH3/MeOH(1.75N)/DCM = 0-20%) to obtain MFH-1-155-1 ( 230 g, yield 56%).LCMS (m/z): 294 [M + H]+.
  • 12
  • [ 4090-55-5 ]
  • [ 3385-21-5 ]
  • C16H32N2O6P2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.3 g With aluminum (III) chloride; In toluene; at 10 - 80℃; for 6h; In a reflux condenser, thermometer, stirrer,Constant pressure dropping funnel 2000mL four-necked flask was added 74g of cyclic phosphorus oxychloride,8 g of anhydrous aluminum trichloride and 800 mL of toluene were added to dissolve them with stirring.Under stirring at 10 C,22.8gBetween cyclohexane diamine four-necked flask,After the addition of cyclohexane diamine is completed,The temperature was raised to 80 C,And the reaction at this temperature 6h, after the reaction was recovered by vacuum distillation solvent,The residue was washed three times with deionized water to give a white solid powder,After drying at 60 C for 10 h, 73.3 g of a product was obtained in a yield of 89.8% by weight.
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